I'm japanese and can't write the solution well.
But for TAer which can't read Japanese, I write this guide.
Matching Maker 4 is quite easy to complete.
This game is made by japanese.
But if you don't know Japanese well, it will be no problem.
First,
You must try to get the points about 500,000pts in story mode.
this game can only get the points while spending times in the game.
So I suggest you set your Controller ( repeat A ) and go to bed everyday.
If you get 500,000pts, make a savedata and back-ups.
Second,
Repeat build the same objects till you get the achievement.It needs 100 objects to get.
If you get an achievement, load and repeat for the another achievement!
third,
Load the savedata.
Finally you can play story mode of this game.
It only requires the population in story mode.
You don't have to build TrainStation, BusStation, Highway, Monorail, boat station, and airport.
For raise population, Build great apartments.This is on rightmost.
And set around other objects of all categories about each 4 apartments.
If you feel the amounts of people don't increase, you build houses with car garage.
At 24:00, you can get the points and have a chance of upgrade.
How to get the upgrade is you must build many objects each days.
At last,
If you are over 3000 of population and reach 24:00, you complete story.
But you continue for "5000 population"achievement.
I hope this guide helps you.